Founders Future

Bridging Startups and Giants: The Bramble and Bird Consulting Model

Closers.io

In this episode of Founders Future, with host Jae Encarnacion, we sit down with Ann Boger, founder of Bramble and Bird Consulting, to explore how she's redefining strategic management for regulated industries like insurance and healthcare. With 20+ years of experience in leadership roles at Coterie and Freelancers Union, Ann shares how witnessing the cyclical layoffs of specialized talent in tech startups inspired her to build a distributed team model that provides fractional C-suite expertise to early-stage ventures. She dives into her unique approach of pairing deep industry knowledge with operational agility—helping funded startups and joint ventures navigate complex regulations while optimizing their legal spend and go-to-market strategies.

Ann also reveals how she's scaling through her Talent Cloud initiative—a vetted network of solopreneurs with niche expertise—and her vision to create an ecosystem bridging innovators with incumbents. From the challenges of founder-led content creation to securing strategic partnerships, she offers candid advice on avoiding burnout, the power of authentic networking ("befriend your 'competition'"), and why self-care is non-negotiable for sustainable growth.